Dataset Information

Antiplasmodial Ealapasamines A-C,'Mixed' Naphthylisoquinoline Dimers from the Central African Liana Ancistrocladus ealaensis.

ABSTRACT: Three unusual heterodimeric naphthylisoquinoline alkaloids, named ealapasamines A-C (1-3), were isolated from the leaves of the tropical plant Ancistrocladus ealaensis J. Léonard. These 'mixed', constitutionally unsymmetric dimers are the first stereochemically fully assigned cross-coupling products of a 5,8'- and a 7,8'-coupled naphthylisoquinoline linked via C-6' in both naphthalene portions. So far, only two other West and Central Ancistrocladus species were known to produce dimers with a central 6,6″-axis, yet, in contrast to the ealapasamines, usually consisting of two 5,8'-coupled monomers, like e.g., in michellamine B. The new dimers 1-3 contain six elements of chirality, four stereogenic centers and the two outer axes, while the central biaryl axis is configurationally unstable. The elucidation of the complete stereostructures of the ealapasamines was achieved by the interplay of spectroscopic methods including HRESIMS, 1D and 2D NMR (in particular ROESY measurements), in combination with chemical (oxidative degradation) and chiroptical (electronic circular dichroism) investigations. The ealapasamines A-C display high antiplasmodial activities with excellent half-maximum inhibition concentration values in the low nanomolar range.

SUBMITTER: Tshitenge DT

PROVIDER: S-EPMC5515985 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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Antiplasmodial Ealapasamines A-C,'Mixed' Naphthylisoquinoline Dimers from the Central African Liana Ancistrocladus ealaensis.

Tshitenge Dieudonné Tshitenge DT Feineis Doris D Mudogo Virima V Kaiser Marcel M Brun Reto R Bringmann Gerhard G

Scientific reports 20170718 1

Three unusual heterodimeric naphthylisoquinoline alkaloids, named ealapasamines A-C (1-3), were isolated from the leaves of the tropical plant Ancistrocladus ealaensis J. Léonard. These 'mixed', constitutionally unsymmetric dimers are the first stereochemically fully assigned cross-coupling products of a 5,8'- and a 7,8'-coupled naphthylisoquinoline linked via C-6' in both naphthalene portions. So far, only two other West and Central Ancistrocladus species were known to produce dimers with a cen ...[more]

PMID: 28720905

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Project description:Lianas are important components of tropical forest diversity and dynamics, yet little is known about the drivers of their community structure and composition. Combining extensive field and LiDAR data, we investigated the influence of local topography, forest structure, and tree composition on liana community structure, and their floristic and functional composition, in a moist forest in northern Republic of Congo. We inventoried all lianas ≥ 1 cm in diameter in 144 20 × 20-m quadrats located in four 9-ha permanent plots, where trees and giant herbs were inventoried. We characterized the functional strategies of selected representatives of the main liana taxa using a set of resource-use leaf and wood traits. Finally, we used complementary statistical analyses, including multivariate and randomization approaches, to test whether forest structure, topography, and tree composition influence the structure, floristic composition, and functional composition of liana communities. The structure of liana communities was strongly shaped by local forest structure, with higher abundances and total basal areas in relatively open-canopy forests, where lianas competed with giant herbs. Liana floristic composition exhibited a weak spatial structure over the study site but was marginally influenced by the local forest structure and topography. Only forest structure had a weak but significant effect on liana functional composition, with more conservative strategies-higher stem tissue density and lower PO4 leaf concentration and SLA values-in tall and dense forests. Finally, we found evidence of host specificity with significant attraction/repulsion for 19% of the tested liana and tree species associations, suggesting that the unexplained floristic variation may be partly attributed to these host-species-specific associations, although the underlying mechanisms behind remain elusive. Overall, our findings demonstrate that liana communities' structure can be much better predicted than their composition, calling for a better understanding of the implications of the large functional diversity observed in liana communities.

Dataset Information

Antiplasmodial Ealapasamines A-C,'Mixed' Naphthylisoquinoline Dimers from the Central African Liana Ancistrocladus ealaensis.

Publications

Antiplasmodial Ealapasamines A-C,'Mixed' Naphthylisoquinoline Dimers from the Central African Liana Ancistrocladus ealaensis.

Similar Datasets

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